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I'm just a bit disappointed that the relationship Keima had with Urara disappeared and this new one doesn't seem like it'll be as close (plus if she keeps thinking he's an alien when this is done, it'll be even worst).

Well...
Maybe the flag for Keima's true end (true world line where Keima comes from) is re-conquest all of his target or atleast the one who hold the goddesses. Since goddess are attracted by love. And for the goddess to be able to host in human, they need a love catalyst. Here little Keima must play his role as a gamer who already know the ending. Putting the goddess to each of the host.

Elsie's illusions are pretty useless huh? Even Keima's low expectations are too high

This is all getting complicated. It's possible that they won't recognize him as the alien and there will be no consequences to their relationships later on, otherwise Yui doing the transition to her manly personality won't work. And this is obviously really important.

Well...
Maybe the flag for Keima's true end (true world line where Keima comes from) is re-conquest all of his target or atleast the one who hold the goddesses. Since goddess are attracted by love. And for the goddess to be able to host in human, they need a love catalyst. Here little Keima must play his role as a gamer who already know the ending. Putting the goddess to each of the host.

The Goddesses aren't even in the girls yet, they only free themselves and find hosts after the demons are freed (like when Diana entered Tenri).

The Goddesses aren't even in the girls yet, they only free themselves and find hosts after the demons are freed (like when Diana entered Tenri).

Yes, I know that. This is just a wild guess. What I mean is that the host of the goddess are not a random target. They are the target that already decided for Keima to be able to go back to his future.

The flag that maybe lead Keima to go back to his future:
- The camping trip
- Earthquake
- The demons freed
- Diana enters Tenri (small)

So, what if all of this events are the result of Keima's action, including the last.

All of flashback in previous Tenri's conquest arc is all planned by Keima:
Keima (small) befriend Tenri (small). Tenri (small) show some affection for Keima (small). The goddess sense this affection (in this case is Diana). Finally, Diana enter Tenri (small).

This also answer why Keima (big) has vague memory of this event when he meet Tenri (big) for the first time.

But, we already know that in the future, the one that send Keima (big) back to the past is not Diana alone. Diana need the help from all of the Jupiter sisters. So, Keima (small) also need to bring each goddess to their respective host. Hence the next flags is:
- Appolo enters Kanon (small)
- Vulcan enters Tsukiyo (small)
- Mars enters Yui (small)
- Minerva enters Shiori (small)
- Mercury enters Ayumi (small)

Here we will see Keima small version doing his conquest to the goddess candidate that coincidentally (or not) are the one that close to Keima.